Chlorotrimethylsilane → HCID 22323650, compound

HRID 2269681Notes

Reaction equation

HRID 2269681 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][OH:8].C[Si](Cl)(C)C.[C:14]1([C:20]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[S:21]Cl)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1.C(Cl)Cl>[OH:1][CH2:2][CH2:3][N:4]([S:21][C:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:5][CH2:6][CH2:7][OH:8]

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 342378Triphenylmethanesulfenyl ChlorideHCID 30150593-((2-Hydroxyethyl)amino)propanol

Product 1

HCID 22323650HCID 22323650, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Procedure

N-(2-hydroxyethyl)-3-amino-1-propanol (5.0 g, 41.9 mmol) is coevaporated several times with pyridine (20 mL) and then dissolved in pyridine (100 mL). The reaction flask is flushed with Argon and trimethylsilylchloride (2.47 g, 209.5 mmol) is added dropwise. The reaction mixture is stirred for 1 hour. Triphenyl methanesulfenyl chloride (14.32 g, 46.09 mmol) is dissolved in CH2Cl2 and added via dropping funnel to the cooled reaction mixture. The reaction mixture is warmed to room temperature and stirred for 18 hours. The reaction mixture is concentrated in vacuo and the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1). The H2O layer is separated and extracted with EtOAc (3×50 ml). The EtOAc extracts are pooled, dried (MgSO4) and filtered. The filtrate is concentrated in vacuo and the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound.

Workup

  1. additionis added dropwise
  2. additionadded
  3. customto the cooled reaction mixture
  4. stirringstirred for 18 hours
  5. concentrationThe reaction mixture is concentrated in vacuo
  6. customthe resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1)
  7. customThe H2O layer is separated
  8. extractionextracted with EtOAc (3×50 ml)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationThe filtrate is concentrated in vacuo
  12. customthe residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea0705d3d39e439a983215f7d015a9b4
Source dataset
uspto-grants-2001_12
Patent number
US06329523B1

Reaction notes

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